CA2223513A1 - Derives d'acide betulinique et leurs utilisations - Google Patents

Derives d'acide betulinique et leurs utilisations

Info

Publication number
CA2223513A1
CA2223513A1 CA002223513A CA2223513A CA2223513A1 CA 2223513 A1 CA2223513 A1 CA 2223513A1 CA 002223513 A CA002223513 A CA 002223513A CA 2223513 A CA2223513 A CA 2223513A CA 2223513 A1 CA2223513 A1 CA 2223513A1
Authority
CA
Canada
Prior art keywords
betulinic acid
substituted
group
acid derivatives
uses therefor
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002223513A
Other languages
English (en)
Other versions
CA2223513C (fr
Inventor
Kuo-Hsiung Lee
Yoshiki Kashiwada
Fumio Hashimoto
Louis Mark Cosentino
Mark Manak
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
University of North Carolina at Chapel Hill
Panacos Pharmaceuticals Inc
Original Assignee
Individual
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of CA2223513A1 publication Critical patent/CA2223513A1/fr
Application granted granted Critical
Publication of CA2223513C publication Critical patent/CA2223513C/fr
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
    • C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Virology (AREA)
  • Emergency Medicine (AREA)
  • Molecular Biology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Steroid Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)
CA002223513A 1995-06-05 1996-06-05 Derives d'acide betulinique et leurs utilisations Expired - Fee Related CA2223513C (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US08/463,071 US5679828A (en) 1995-06-05 1995-06-05 Betulinic acid and dihydrobetulinic acid derivatives and uses therefor
US08/463,071 1995-06-05
PCT/US1996/009485 WO1996039033A1 (fr) 1995-06-05 1996-06-05 Derives d'acide betulinique et leurs utilisations

Publications (2)

Publication Number Publication Date
CA2223513A1 true CA2223513A1 (fr) 1996-12-12
CA2223513C CA2223513C (fr) 2009-03-24

Family

ID=23838749

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002223513A Expired - Fee Related CA2223513C (fr) 1995-06-05 1996-06-05 Derives d'acide betulinique et leurs utilisations

Country Status (10)

Country Link
US (1) US5679828A (fr)
EP (2) EP1397957A2 (fr)
AT (1) ATE275823T1 (fr)
AU (1) AU6328896A (fr)
CA (1) CA2223513C (fr)
DE (1) DE69633398T8 (fr)
DK (1) DK0857018T3 (fr)
ES (1) ES2231818T3 (fr)
PT (1) PT857018E (fr)
WO (1) WO1996039033A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9067966B2 (en) 2009-07-14 2015-06-30 Hetero Research Foundation, Hetero Drugs Ltd. Lupeol-type triterpene derivatives as antivirals
US9637516B2 (en) 2012-12-31 2017-05-02 Hetero Research Foundation Betulinic acid proline derivatives as HIV inhibitors
US9868758B2 (en) 2014-06-30 2018-01-16 Hetero Labs Limited Betulinic proline imidazole derivatives as HIV inhibitors
US10370405B2 (en) 2015-03-16 2019-08-06 Hetero Labs Limited C-3 novel triterpenone with C-28 amide derivatives as HIV inhibitors
US10533035B2 (en) 2015-02-09 2020-01-14 Hetero Labs Ltd. C-3 novel triterpenone with C-17 reverse amide derivatives as HIV inhibitors

Families Citing this family (54)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5962527A (en) * 1995-03-21 1999-10-05 The Board Of Trustees Of The University Of Illinois Method and composition for treating cancers
US5869535A (en) * 1995-03-21 1999-02-09 The Board Of Trustees Of The University Of Illinois Method and composition for selectively inhibiting melanoma
WO1998032443A1 (fr) * 1997-01-24 1998-07-30 Marigen S.A. Ultramicro-emulsions de concentres spontanement dispersibles renfermant des esters de triterpenes pentacycliques a activite antitumorale, antivirale et antiparasitaire
US5750578A (en) * 1997-02-11 1998-05-12 Regents Of The University Of Minnesota Use of betulin and analogs thereof to treat herpesvirus infection
US6890533B2 (en) * 1997-06-04 2005-05-10 Cornell Research Foundation, Inc. Betulinol derivatives
US6228850B1 (en) * 1997-09-30 2001-05-08 Dabur Research Foundation Antiangiogenic activity of betulinic acid and its derivatives
US6670345B1 (en) * 1997-09-30 2003-12-30 Dabur Research Foundation Betulinic acid derivatives for inhabiting cancer growth and process for the manufacture of betulinic acid
US6048847A (en) * 1997-09-30 2000-04-11 Dabur Research Foundation Use of betulinic acid and its derivatives for inhibiting cancer growth and a method of monitoring this
CA2322868C (fr) * 1998-03-02 2009-02-03 The University Of North Carolina At Chapel Hill Derives acyles de betuline et de dihydrobetuline, leur preparation, et leur utilisation
US6303589B1 (en) * 1998-12-08 2001-10-16 Micro Flo Company Pentacyclic triterpenes
US6369101B1 (en) 1999-02-26 2002-04-09 Regents Of The University Of Minnesota Therapeutic method to treat herpes virus infection
US6392070B1 (en) 1999-08-10 2002-05-21 Regents Of The University Of Minnesota Birch bark processing and the isolation of natural products from birch bark
DE69917684T2 (de) * 1999-09-09 2005-07-21 Dabur Research Foundation, Sahibabad Betulinsäure-derivate mit antiangiogener wirkung, verfahren zur herstellung solcher derivate und deren verwendung für die behandlung tumorassoziierter angiogenese
WO2002091858A1 (fr) * 2001-05-11 2002-11-21 University Of Ottawa Compositions anxiolytiques de marcgraviaceae contenant de l'acide betulinique ou des derives d'acide betulinique et procedes associes
NZ538896A (en) * 2002-09-26 2007-10-26 Niigata University Of Pharmacy Monoacylated betulin and dihydrobetulin derivatives, preparation thereof and use thereof
US7365221B2 (en) * 2002-09-26 2008-04-29 Panacos Pharmaceuticals, Inc. Monoacylated betulin and dihydrobetulin derivatives, preparation thereof and use thereof
US7537765B2 (en) * 2003-01-29 2009-05-26 Panacos Pharmaceuticals, Inc. Inhibition of HIV-1 replication by disruption of the processing of the viral capsid-spacer peptide 1 protein
CA2514563A1 (fr) * 2003-01-29 2004-08-19 Panacos Pharmaceuticals, Inc. Inhibition de la replication du vih-1 par interruption du traitement de la proteine capside-peptide espaceur 1 virale
US7026305B2 (en) * 2003-04-14 2006-04-11 Meharry Medical College Anti-HIV agents with dual sites of action
US20050239748A1 (en) * 2004-03-17 2005-10-27 Panacos Pharmaceuticals, Inc. Pharmaceutical salts of 3-O-(3',3'-dimethylsuccinyl) betulinic acid
ZA200608624B (en) * 2004-03-17 2008-05-28 Panacos Pharmaceuticals Inc Pharmaceutical salts of 3-0(3',3'-dimethylsuccinyl) betulinic acid
US20060019934A1 (en) * 2004-05-20 2006-01-26 Saxena Brij B Anti-HIV-1 activity of betulinol derivatives
BRPI0511514A (pt) * 2004-05-24 2008-08-05 Panacos Pharmaceuticals Inc inibição da replicação de hiv-1 por ruptura do processamento da proteìna de peptìdeo capsìdeo-espaçador 1 viral
CA2580076A1 (fr) 2004-09-10 2006-03-23 Cornell Research Foundation, Inc Derives de betulinol utilises en tant qu'agents anti-vih
TW200628161A (en) * 2004-11-12 2006-08-16 Panacos Pharmaceuticals Inc Novel betulin derivatives, preparation thereof and use thereof
BRPI0610668A2 (pt) 2005-04-12 2010-07-13 Panacos Pharmaceuticals Inc polimorfas de di-n-metil-d-glucamina do ácido 3-o-(3',3'-dimetilsuccinil) betulìnico
WO2007002411A1 (fr) * 2005-06-22 2007-01-04 Myriad Genetics, Inc. Composés antiviraux
CN101374527A (zh) * 2005-12-16 2009-02-25 帕纳克斯医药公司 3-o-(3’,3’-二甲基琥珀酰基)桦木酸的药物盐的制备方法
WO2007114978A2 (fr) * 2006-02-09 2007-10-11 Boehringer Ingelheim International Gmbh Procédé destiné à traiter une infection au vih par une administration conjointe de tipranavir et de pa-457
EP1996205A2 (fr) * 2006-03-23 2008-12-03 Advanced Life Sciences Inc. Triterpenoides pentacycliques synthetiques et derives d'acide betulinique et de betuline
US20080039428A1 (en) * 2006-06-29 2008-02-14 Panacos Pharmaceuticals, Inc. Antiretroviral combination therapy
WO2008115281A2 (fr) * 2006-10-16 2008-09-25 Myriad Genetics, Inc. Composés de traitement d'infections virales
AR063546A1 (es) 2006-11-03 2009-01-28 Panacos Pharmaceuticals Inc DERIVADOS DE TRITERPENO, METODOS PARA SU PREPARACION, COMPOSICIONES FARMACEUTICAS QUE LOS COMPRENDEN Y SU USO EN LA FABRICACION DE MEDICAMENTOS PARA EL TRATAMIENTO DE INFECCIoN POR EL VIRUS VIH.
US20110152229A1 (en) * 2006-11-22 2011-06-23 Duke University Betulinic acid derivatives as anti-hiv agents
US8802661B2 (en) 2010-06-04 2014-08-12 Bristol-Myers Squibb Company C-28 amides of modified C-3 betulinic acid derivatives as HIV maturation inhibitors
CA2801487C (fr) 2010-06-04 2017-12-05 Bristol-Myers Squibb Company Derives d'acide betulinique modifies en c-3, utilises comme inhibiteurs de maturation du vih
RU2448115C1 (ru) * 2010-12-20 2012-04-20 Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Новосибирский национальный исследовательский государственный университет" (Новосибирский государственный университет (НГУ) Гидрированная бетулоновая кислота и ее амиды как противоопухолевые средства тритерпеновой природы
RS54352B1 (en) 2011-01-31 2016-02-29 Bristol-Myers Squibb Company C-28 AMINES OF C-3 MODIFIED BETULINIC ACID DERIVATIVES AS HIV INVESTIGATION INHIBITORS
CA2826113C (fr) 2011-01-31 2018-09-04 Bristol-Myers Squibb Company Triterpenoides modifies en c-17 et c-3 presentant une activite inhibitrice de la maturation du vih
KR20140069167A (ko) 2011-09-21 2014-06-09 브리스톨-마이어스 스큅 컴퍼니 항바이러스 활성을 갖는 신규 베툴린산 유도체
US8906889B2 (en) 2012-02-15 2014-12-09 Bristol-Myers Squibb Company C-3 cycloalkenyl triterpenoids with HIV maturation inhibitory activity
US8889854B2 (en) 2012-05-07 2014-11-18 Bristol-Myers Squibb Company C-17 bicyclic amines of triterpenoids with HIV maturation inhibitory activity
CN103768078B (zh) 2012-10-22 2019-02-05 北京大学 三萜衍生物及其抗流感用途
EP2953960A1 (fr) 2013-02-06 2015-12-16 Bristol-Myers Squibb Company Triterpénoïdes modifiés en c-19 ayant une activité inhibant la maturation du vih
CN105102468A (zh) 2013-02-25 2015-11-25 百时美施贵宝公司 用于治疗hiv的c-3烷基和烯基修饰的桦木酸衍生物
CA2944778C (fr) 2014-04-11 2022-06-14 ViiV Healthcare UK (No.4) Limited Triterpenes a activite d'inhibition de la maturation du vih
WO2015195776A1 (fr) 2014-06-19 2015-12-23 Bristol-Myers Squibb Company Dérivés d'acide bétulinique présentant une activité inhibitrice de maturation du vih
KR20170092581A (ko) 2014-11-14 2017-08-11 비브 헬스케어 유케이 (넘버5) 리미티드 Ｃ１７-아릴 치환된 베툴린산 유사체
US9969767B2 (en) 2014-11-14 2018-05-15 VIIV Healthcare UK (No.5) Limited Oxolupene derivatives
PL227790B1 (pl) 2015-08-13 2018-01-31 Slaski Univ Medyczny W Katowicach Fosfoniany acetylenowych pochodnych betuliny o działaniu przeciwnowotworowym, sposób ich wytwarzania i zastosowanie.
AR107512A1 (es) 2016-02-04 2018-05-09 VIIV HEALTHCARE UK Nº 5 LTD Triterpenoides modificados en c-3 y c-17 como inhibidores del vih-1
US20220296610A1 (en) * 2017-04-06 2022-09-22 Derm-Biome Pharmaceuticals Inc. Compositions and methods for treatment of infection and novel cosmeceutical preparations
PL237998B1 (pl) 2018-05-28 2021-06-28 Narodowy Inst Lekow Fosfonowe pochodne kwasu 3-karboksyacylobetulinowego, sposób ich otrzymywania oraz ich zastosowanie
CA3101643C (fr) 2018-06-29 2023-02-21 Dfh Therapeutics Derives d'amine triterpenique

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1415601A (en) * 1973-03-14 1975-11-26 Biorex Laboratories Ltd Dihydrobetulinic acid derivatives
FR2683531B1 (fr) * 1991-11-13 1993-12-31 Rhone Poulenc Rorer Sa Nouveaux derives du lupane, leur preparation et les compositions pharmaceutiques qui les contiennent.
US5643884A (en) * 1993-08-09 1997-07-01 Glycomed Incorporated Lupane triterpenoid derivatives

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9067966B2 (en) 2009-07-14 2015-06-30 Hetero Research Foundation, Hetero Drugs Ltd. Lupeol-type triterpene derivatives as antivirals
US9637516B2 (en) 2012-12-31 2017-05-02 Hetero Research Foundation Betulinic acid proline derivatives as HIV inhibitors
US9868758B2 (en) 2014-06-30 2018-01-16 Hetero Labs Limited Betulinic proline imidazole derivatives as HIV inhibitors
US10533035B2 (en) 2015-02-09 2020-01-14 Hetero Labs Ltd. C-3 novel triterpenone with C-17 reverse amide derivatives as HIV inhibitors
US11034718B2 (en) 2015-02-09 2021-06-15 Hetero Labs Limited C-3 novel triterpenone with C-17 reverse amide derivatives as HIV inhibitors
US10370405B2 (en) 2015-03-16 2019-08-06 Hetero Labs Limited C-3 novel triterpenone with C-28 amide derivatives as HIV inhibitors

Also Published As

Publication number Publication date
DK0857018T3 (da) 2004-11-29
US5679828A (en) 1997-10-21
EP0857018A4 (fr) 2002-10-23
EP0857018B1 (fr) 2004-09-15
AU6328896A (en) 1996-12-24
ES2231818T3 (es) 2005-05-16
DE69633398T8 (de) 2006-01-12
EP1397957A2 (fr) 2004-03-17
PT857018E (pt) 2005-01-31
WO1996039033A1 (fr) 1996-12-12
EP0857018A1 (fr) 1998-08-12
DE69633398D1 (de) 2004-10-21
DE69633398T2 (de) 2005-09-22
CA2223513C (fr) 2009-03-24
ATE275823T1 (de) 2004-10-15

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